We have researched and purchased the best options for us on the trail.  Some new additions to our arsenal are:  Zpacks Duomid tent, Thermarest Xlite sleeping pad, Bear Vault 500 bear can, Loco Libre Ghostpepper topquilt, Osprey Exos 58 Pack, SOG Traction Tanto, and a Gerber BG Scout.  Some of these items were purchased back in Alaska and the others while in Florida and Thailand.  When we researched additions for our gear, my main concern was Dollars per Ounce.  How much did the ounce of savings cost us?  What I would do was take the cost of the item and divide it by the total weight savings for replacing it.  ($/oz)

For Example:

I’ve been looking at getting the Montbell Superior Down Round Jacket for some time and it would cost me $125.  I’ve also been thinking about the Zpacks Arc Haul backpack, costing $389.  They both save me approximately 9.5oz.

Jacket   $125 / 9.5oz = $13.16/oz (The cheaper option to upgrade)
Pack    $389 / 9.6oz = $41.38/oz

Logic would say that I should purchase the jacket before the pack.  It is not always about cost.  The more expensive item doesn’t always have a higher $/oz value.

For Sierra, her pack would cost $344 for the Arc Haul, with a savings of 12.5oz.  Her stuff sacks, to upgrade to Cuben Fibre, would cost $82 for a savings of 1.2oz.

Pack     $344 / 12.5oz = $27.52/oz (Cheaper than my pack)
Stuff Sacks    $82 / 1.2oz = $68.33/oz (More expensive than my pack)

This is how we determine which gear to upgrade and when.  Sometimes the bigger purchase is more worth it and sometimes the smaller things are.  I hope this helps you to strategically upgrade your gear in a more cost effective way.